Hydrochloric Acid → HCID 178439475, compound

HRID 449885Notes

Reaction equation

HRID 449885 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[CH3:5][CH:6]([CH3:14])[C:7](=O)[CH2:8][C:9](OC)=[O:10].C([O-])([O-])=O.[K+].[K+].Cl>O.CO>[CH:6]([C:7]1[N:4]=[C:2]([SH:3])[N:1]=[C:9]([OH:10])[CH:8]=1)([CH3:14])[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 2759969Methyl 4-methyl-3-oxopentanoate

Product 1

HCID 178439475HCID 178439475, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
105 °C

Procedure

Thiourea (1.0 g, 13 mmol) was dissolved in 1.6 mL of water at 70° C. Methyl 4-methyl-3-oxopentanoate (2.8 g, 20 mmol) was added and followed by K2CO3 (2.7 g, 19 mmol). The reaction was heated at 105° C. open to air for 1 hour to boil off any remaining methanol. After being cooled to room temperature, water (6.6 mL) was added and followed by 6 mL of concentrated HCl. The white precipitate was collected by filtration and washed with water and 1 N HCl to afford 6-isopropyl-2-mercaptopyrimidin-4-ol as a white solid (1.5 g, yield: 46%). 1H NMR (400 MHz, DMSO-d6): δ 12.34 (s, 1H), 12.19 (s, 1H), 5.67 (s, 1H), 2.66 (m, 1H), 1.13 (d, J=6.8 Hz, 6H). LCMS (ESI) m/z: 171.0 [M+H+].

Workup

  1. temperatureAfter being cooled to room temperature
  2. filtrationThe white precipitate was collected by filtration
  3. washwashed with water and 1 N HCl

Sources & evidence

ORD record
ord-aac8fac1c0a04fe59d32d24eaed357f3
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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